3-Aminopyridine → 1-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 75444Notes

Reaction equation

HRID 75444 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[C:2]=[O:3].[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=1>C1(C)C=CC=CC=1.O1CCCC1>[N:19]1[CH:24]=[CH:23][CH:22]=[C:21]([NH:25][C:2]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([B:10]3[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]3)=[CH:6][CH:5]=2)=[O:3])[CH:20]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 446075271-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

1-(Pyridin-3-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea was prepared by treatment of 2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (50, 2.50 g, 10.20 mmoles) in toluene/tetrahydrofuran (3:1) with pyridine-3-amine (51, 0.960 g, 10.20 mmoles). The reaction mixture was stirred at room temperature for 16 hours, then concentrated. Yield: 3.21 g (93%). LCMS (HP walk-on); 2.89 min., 340.6, M+H.

Workup

  1. concentrationconcentrated
  2. custom2.89 min., 340.6, M+H

Sources & evidence

ORD record
ord-d8fd8883c1fe43ef98c6f58e3053c2ad
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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